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865466-24-6

865466-24-6 structure
865466-24-6 structure
  • Name: Narlaprevir
  • Chemical Name: (1R,2S,5S)-3-[(2S)-2-[[1-(tert-butylsulfonylmethyl)cyclohexyl]carbamoylamino]-3,3-dimethylbutanoyl]-N-[(3S)-1-(cyclopropylamino)-1,2-dioxoheptan-3-yl]-6,6-dimethyl-3-azabicyclo[3.1.0]hexane-2-carboxamide
  • CAS Number: 865466-24-6
  • Molecular Formula: C36H61N5O7S
  • Molecular Weight: 707.964
  • Catalog: Signaling Pathways Anti-infection HCV
  • Create Date: 2018-12-21 15:42:22
  • Modify Date: 2024-01-02 19:51:11
  • Narlaprevir is a potent, selective, orally bioavailable NS3 protease inhibitor(Ki=6 nM; EC90=40 nM)IC50 Value: 6 nM (Ki)Target: HCV NS3/4A Protease; HCVNarlaprevir (SCH 900518) is a potent inhibitor of the hepatitis C virus (HCV) nonstructural protein 3 serine protease that is primarily metabolized by the cytochrome P450-3A4 system. Narlaprevir administration resulted in a robust HCV-RNA decline and high SVR rates when followed by standard of care in both treatment-experienced and treatment-naive HCV genotype 1-infected patients.

Name (1R,2S,5S)-3-[(2S)-2-[[1-(tert-butylsulfonylmethyl)cyclohexyl]carbamoylamino]-3,3-dimethylbutanoyl]-N-[(3S)-1-(cyclopropylamino)-1,2-dioxoheptan-3-yl]-6,6-dimethyl-3-azabicyclo[3.1.0]hexane-2-carboxamide
Synonyms (1R,2S,5S)-3-((S)-2-(3-(1-(tert-butylsulfonylmethyl)cyclohexyl)ureido)-3,3-dimethylbutanoyl)-N-((S)-1-(cyclopropylamino)-1,2-dioxoheptan-3-yl)-6,6-dimethyl-3-azabicyclo[3.1.0]hexane-2-carboxamide
(1R,2S,5S)-N-[(3S)-1-(Cyclopropylamino)-1,2-dioxo-3-heptanyl]-6,6-dimethyl-3-{3-methyl-N-[(1-{[(2-methyl-2-propanyl)sulfonyl]methyl}cyclohexyl)carbamoyl]-L-valyl}-3-azabicyclo[3.1.0]hexane-2-carboxamide
CS-0445
Narlaprevir (USAN/INN)
Narlaprevir
(1R,5S)-N-[1(S)-[2-(cyclopropylamino)-1,2-dioxoethyl]pentyl]-3-[2(S)-[[[[1-[[(1,1-dimethylethyl)sulfonyl]methyl]cyclohexyl]amino]carbonyl]amino]-3,3-dimethyl-1-oxobutyl]-6,6-dimethyl-3-azabicyclo[3.1.0]hexane-2(S)-carboxamide
3-Azabicyclo[3.1.0]hexane-2-carboxamide, N-[(1S)-1-[2-(cyclopropylamino)-1,2-dioxoethyl]pentyl]-3-[(2S)-2-[[[[1-[[(1,1-dimethylethyl)sulfonyl]methyl]cyclohexyl]amino]carbonyl]amino]-3,3-dimethyl-1-oxobutyl]-6,6-dimethyl-, (1R,2S,5S)-
Description Narlaprevir is a potent, selective, orally bioavailable NS3 protease inhibitor(Ki=6 nM; EC90=40 nM)IC50 Value: 6 nM (Ki)Target: HCV NS3/4A Protease; HCVNarlaprevir (SCH 900518) is a potent inhibitor of the hepatitis C virus (HCV) nonstructural protein 3 serine protease that is primarily metabolized by the cytochrome P450-3A4 system. Narlaprevir administration resulted in a robust HCV-RNA decline and high SVR rates when followed by standard of care in both treatment-experienced and treatment-naive HCV genotype 1-infected patients.
Related Catalog
References

[1]. Ashok Arasappan, et al. Discovery of Narlaprevir (SCH 900518): A Potent, Second Generation HCV NS3 Serine Protease Inhibitor. ACS Med. Chem. Lett., 2010, 1 (2), pp 64–69

[2]. Tong X, Arasappan A, Bennett F, Chase R, Feld B, Guo Z, Hart A, Madison V, Malcolm B, Pichardo J, Prongay A, Ralston R, Skelton A, Xia E, Zhang R, Njoroge FG.Preclinical characterization of the antiviral activity of SCH 900518 (narlaprevir), a novel mechanism-based inhibitor of hepatitis C virus NS3 protease.Antimicrob Agents Chemother. 2010 Jun;54(6):2365-70. Epub 2010 Mar 22.

[3]. Zhu J, Li Y, Yu H, Zhang L, Mao X, Hou T.Insight into the structural requirements of narlaprevir-type inhibitors of NS3/NS4A protease based on HQSAR and molecular field analyses.Comb Chem High Throughput Screen. 2012 Jul;15(6):439-50.

[4]. de Bruijne J, Bergmann JF, Reesink HW, Weegink CJ, Molenkamp R, Schinkel J, Tong X, Li J, Treitel MA, Hughes EA, van Lier JJ, van Vliet AA, Janssen HL, de Knegt RJ.Antiviral activity of narlaprevir combined with ritonavir and pegylated interferon in chronic hepatitis C patients.Hepatology. 2010 Nov;52(5):1590-9.

[5]. Tomillero A, Moral MA.Gateways to clinical trials.Methods Find Exp Clin Pharmacol. 2010 Nov;32(9):675-703.

Density 1.2±0.1 g/cm3
Molecular Formula C36H61N5O7S
Molecular Weight 707.964
Exact Mass 707.429199
PSA 186.21000
LogP 3.61
Index of Refraction 1.558